Patent GB-1095815-A (GB)
Title: Bisphenol polyesters
Inventor: SWEENY WILFRED
IPC: C08G63/40
Filed: 1966-01-06
Abstract: A fibre-forming polyester consists essentially of recurring units <FORM:1095815/C3/1> wherein Ar is a substituted or unsubstituted m-or p-phenylene group, n is 0 or 1, X is halogen or a Cl-6 alkoxy group, Y is halogen or a Cl-6 alkoxy group, or may be H if X is halogen, and Z is -CRR1-, -O-, -SO2-or <FORM:1095815/C3/2> wherein R and R1 are each H or a Cl-6 alkyl group and R11 is an alkylene group of up to 6 C atoms, and has an inherent viscosity of at least 0.5, measured at 30 DEG  C. using 0.5 gm. of polymer in 100 mls. of solution in 60/40 tetrachlorethane/ phenol solvent.  Preferably, X and Y are each Cl, n is 1, Ar is m-phenylene and Z is -O- or -SO2- or -C(CH3)2-.  The polyester may be prepared by reaction of the bisphenol <FORM:1095815/C3/3> with the diacid halide X-CO-Ar-CO-X. This may be done (a) by interphase condensation i.p.o. a catalyst, or (b) by solution polymerization in e.g. cyclopentanone, cyclohexanone, THF or tetrahydropyran, i.p.o. an acid acceptor, e.g. a tertiary amine. Process (a) may be performed using an alkaline aqueous solvent for the bisphenol, and a polymer-solvating organic solvent for the acid, with quaternary ammonium, phosphonium, sulphonium or hydrazinium salts or hydroxides as catalyst, usually at temperatures between 0 DEG  C. and room temperature.  Process (b) operates at e.g. -10 to 185 DEG  C.  Up to 10 wt. per cent of the polymer may derive from reactants other than the above.  Specific bisphenols mentioned include those in which X and Y are each Cl or Br or MeO- or X is Cl or Br while Y is H, while Z is isopropylidene, and the analogues in which Z is methylene, ethylidene, propylidene, n-butylidene, isobutylidene, sec-butylidene, cyclohexylidene, oxygen, sulphone or a direct linking bond.  Preferred acid halides are isophthaloyl and terephthaloyl chlorides and mixtures thereof, 2,5-dichloroterephthaloyl, 5-t-butylisophthaloyl, and 2-, 4- and 5-chloroisophthaloyl chlorides.  Shaped articles may be prepared by extruding a solution of the polyester into a coagulating medium, e.g. water, or mixtures of water with the reaction solvent, or acetone or low molecular weight alcohols.  In examples the interfacial process (a) is carried out using 5N NaOH and 1:1:2 trichlorethane or THF as solvents i.p.o. tetraethylammonium chloride, the solution process (b) is conducted in chloroform, o-dichlorbenzene, THF or cyclohexanone, i.p.o. triethylamine or at 200 DEG  C., and coagulants used are water, acetone, and hexane. Materials used are 4:41-isopropylidenebis (2:6-dichlorophenol) and also bisphenols in which Y = H, X = Cl or Y = X = Br and Z= isopropylidene, and Y = X = Cl and Z is a bond, isobutylidene, cyclohexylidene, oxygen or sulphone; isophthaloyl chloride, isophthaloyl/ terephthaloyl chloride mixtures, 5-chloroisophthaloyl chloride, 2:5-dichloroterephthaloyl chloride and 5-t-butylisophthaloyl chloride.  The products are soluble in chloroform, THF, trichlorethane/ trifluoracetic acid and trichlorethane/phenol.ALSO:Fabrics may be prepared from a polyester of a substituted or unsubstituted isophthalic or terephthalic acid and a bisphenol <FORM:1095815/D1-D2/1> wherein n is 0 or 1, X is halogen or a C1-6 alkoxy group and Y is halogen or a Cl-6 alkoxy group, or may be H is X is halogen, and Z is -O-, -SO2- or an alklidene or cycloalkylidene group (see Division C3).  Such fabrics may be finished by heating them for 4 minutes at 230-235 DEG C, permitting 3% warp and 5% fill shrinkage, followed by taut treatment for 1 hour in boiling aqueous 10% sodium hydroxide.  Poplin fabrics may be prepared from a yarn spun from 35% Egyptian cotton staple and 65% of a staple of the above polyester.ALSO:Fire-resistant coatings for wood or metal may comprise a polyester of a substituted or unsubstituted isophthalic or terephthalic acid and a bisphenol: <FORM:1095815/B1-B2/1> wherein X and Y may be halogen or alkoxy groups, or Y may be H if X is halogen, n = 0 or 1, Z alkylidene, cycloalkylidene, -0- or SO2- (see Division C3).